September 2019 Chicago Events Guide

 September is the perfect time to be in Chicago. The weather is a beautiful combination of cooling and comfortable. The city is still alive and well with plenty of things to do throughout the fall season. The September Chicago events guide highlights the best things to check out this month. Full guide of things to do during September below.


Chicago Men’s Fashion Awards 2019

Tuesday | September 17th | 6:00 p.m. – 9:00 p.m.

Louis Vuitton Michigan Ave | 919 N Michigan Ave. | $85

The Costume Council of the Chicago History Museum is back this month for their annual Chicago Men’s Fashion Awards. The premier men’s fashion event for all enthusiasts. Meet Chicago’s Most Stylish men and enjoy an elegant evening of fun. For tickets to the event, visit Chicago

BIDE Market

Sunday | September 15th | 10:00 a.m. – 4:00 p.m.

Exchange312 | 1714 W Division St. | Free

Image | BIDE Market

This month, experience Chicago’s first sustainable, luxury shopping experience. BIDE Market is fully sustainable, plastic-free, vegan, and cruelty-free. The opening market day will include talks on sustainability as well as food and drinks from ethical brands, including those based in Chicago. To learn more about the sustainable market, visit the website here. 

Ref Chicago Opening Party

Thursday | September 5th | 6:00 p.m. – 8:00 p.m.

Reformation | 56 E Walton St. | Free

Reformation Clothing store as featured on The Haute Seekers September 2019 Chicago Events Guide
Image | Reformation

Reformation makes sustainable women’s clothing and accessories for women of all sizes. The eco-friendly clothing company celebrates the launch of its Chicago store this September. Visit the store for limited-edition totes and tees, music by DJ Jamie Hayes, wine by Winc, and a photo booth. RSVP here for the celebration.

Midwest Flair Fest

Sunday | September 22nd | 11:00 a.m. – 4:00 p.m.

Thalia Hall | 1807 S Allport St. | Free

Image | Midwest Flair Fest

Midwest Flair Fest is a gathering of all things flair. The market features over 40 vendors from all over the US. The flair includes pins, patches, apparel and more. The event is free for all ages. Arrive early and receive a free tote bag filled with swag from the various vendors participating in the event. For more details on this event, visit the event page here.

Food + Drink:

Chicago Gourmet

Saturday – Sunday | September 28th – 29th | Time Varies

Millennium Park | 201 E. Randolph St. | $0 – $2,015

Chicago Gourmet as featured on The Haute Seekers September 2019 Chicago Events Guide
Image | Chicago Gourmet

Chicago Gourmet is one of Septembers biggest food events. As shared in the guide of 31 events to check out this fall, the two-day exhibition features some of the best restaurants, and chefs both locally and from around the world. This year’s theme is inspired by movies, television, and theater and honors Chicago’s culinary achievements and the creative vision chefs, Master Sommeliers, and wine and spirit makers who participate. For tickets and more event details, visit Chicago 

¡Buen Provecho! Taste of Pilsen

Tuesday | September 24th | 5:00 p.m. – 8:30 p.m.

Plaza Tenochtitlan | 1800 S. Blue Island Ave. | $20 – $25

Image | Economic Strategies Development Corporation

Get a taste of some of the best restaurants in Pilsen. The Southwest Side neighborhood hosts Taste of Pilsen this September. Sample eats from over 25 local restaurants, cafes, and bakeries participating in the restaurant tour, providing visitors with their delectable dish. Enjoy a weekday event that celebrates diverse restaurants in the Pilsen neighborhood. For more details, visit the event page.

Taste Of Haiti Chicago 2019

Saturday| September 28th | 11:00 a.m.

Kizin Creole Restaurant | 2311 West Howard St. | 12:00 p.m. – 11:00 p.m.

Image | Kizin Creole Restuarant

Experience a day of Haitian culture at the Taste of Haiti this September. Kizin Creole, the only Haitian restaurant in the city of Chicago is located on the Northside of the city. The annual Taste of Haiti event gives guests the ultimate experience of fine Haitian cuisine, music, and arts. Experience off-menu eats, cooking demos, family activities and more. To learn more about this Taste of Haiti, visit the event page here.

The Whiskey Extravaganza

Friday | September 13th | 7:30 p.m. – 10:00 p.m.

Revel Space | 1215 W Fulton Market St. | $95 – $195

Image | The Whiskey Extravaganza

While the summer is for Rose, the fall is for Whiskey. Sample over 100+ of the world’s best whiskeys at the Whiskey Extravaganza. The event will feature expert masterclasses, whiskey inspired bites, craft cocktails, and more. For tickets and more details on this event, visit the website here.


Chicago Black Social Culture Map: Sounds & Spaces / Westside Edition

Saturday | September 7th | 12:00 p.m. – 6:00 p.m.

West Side Justice Center | 601 S California Ave. | Free

Image | Chicago Black Social Culture Map

Experience Chicago music—the Westside way. This September, the Westside Justice Center will host a community-backed installation that focuses on the development of nightlife and social spaces on Chicago’s Westside. Panels will explore the impact of Westside Blues; the importance of Westside record stores and record labels such as George’s Music Room, Barney’s Music, and Dance Mania Records; and the Westside’s contributions to Chicago House, Footwork, and Juke music and dance cultures. These explorations will be kept on an online public humanities document known as the Chicago Black Social Culture Map. For more details on this community music event, visit the event page.

Soap Box Ball 2019: City Bureau’s Biggest Party of the Year

Thursday | September 19th | 6:00 p.m. – 10:00 p.m.

Glessner House | 1800 S Prairie Ave. | $100 – $125

This month, get on your soapbox. Join City Bureau for their 2019 Soap Box Ball. This year’s derby takes place at the historic Glessner House and features poetry, music, spoken word, and a live DJ throughout the evening. Of course, there will be food and libations to enjoy throughout. Support local journalism at this annual celebration. For tickets, visit the event page.

The 6th Annual City of Big Dreams Fundraiser

Thursday | September 12th | 7:00 p.m.

The Chop Shop & 1st Ward | 2033 West North Ave. | $10 – $115

Image | The Simple Good

Support The Simple Good and their mission to empower at-risk youth through art this September. This month, the non-profit organization presents its 6th Annual “City of Big Dreams” – a collaborative showcase uniting different mediums of art under a single inspiration. Art, music and more will take place during this philanthropical event. For more details and to purchase tickets, visit the event page.

Arts + Culture:

Mid-Autumn Festival

Saturday | September 14th | 5:00 p.m. – 8:00 p.m.

607-647 E 31st St | Free

Image | Chinese American Museum of Chicago

Mid-Autumn Festival, also known as The Chinese Moon Festival, is a traditional event celebrated within the Chinese community. During the festival, guests will have the opportunity to plant a prairie, make lanterns and other forms of art, storytelling, music, a lantern parade, and of course enjoy traditional Mooncakes. This September event is perfect for Chicago families. For more details, visit the event page. 

Chance The Rapper: The Big Day – Plus Special Guests

Saturday | September 28th | 7:00 p.m.

United Center | 1901 W Madison St. | $59 – $149.50

Image | Chance the Rapper

Chicago’s native son Chance the Rapper will perform in one of the cities biggest venues this September. On the heels of his album release The Big Day, the rapper will take the big stage at the United Center to perform songs from his latest album and most likely, hits from his highly acclaimed mixtapes. To purchase tickets to the concert visit

50th Mexican Independence Parade

Sunday | September 8th | 10:00 a.m. – 4:00 p.m.

Kedzie & 26th St. to Kostner & 26th St. | Little Village | Free

Image | La Villita Chamber of Commerce

Celebrate 50 years of the Mexican Independence Parade in Chicago. A spectacular display of lively and colorful floats will take over the Little Village neighborhood this September. This year’s theme is, ‘Celebrando Raices’ exploring the Indigenous roots of Mexican culture. The celebration includes a festival with two stages of live music, a wide variety of authentic food and more at one the largest carnivals in the Midwest. For more details visit the event page.

Creative Chicago: The State of Arts and Culture in Chicago

Saturday | September 14th | 12:00 p.m. – 1:30 p.m.

Venue SIX10| 610 S Michigan Ave. | Free

Image | Art Design Chicago

Creative Chicago, as part of the Terra Foundation’s initiative Art Design Chicago and during Chicago Humanities Festival, is back again. Through conversations and workshop, Creative Chicago gatherers the most influential artists and founders to explore the question, “What is the power of art in addressing the issues affecting our city?” Creative Chicago is free and open to the public. Tickets for the free panel discussion are available here.

This list contains only a few of the great events happening in Chicago. Find other great events by checking out the ultimate fall guide.


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